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This classic 1980's New Zealand ad for BASF cassette tapes features a soldier receiving a version of the country song "Dear John" sung by his fiance on a BASF tape, with some new lyrics turning it into a straight example, leading to the tagline:

Kimi No Iru Machi's Yuzuki writes one to Haruto and puts it in a present she gave him, however it was several months (and several attempts to stay with her regardless) later that he actually found and read the letter.

In Casablanca, Rick and his lover, Ilsa, were supposed to meet at the train station to get out of Paris before the Nazis arrived; instead, she sent a letter explaining that she couldn't be with him, for unexplained reasons. Years later they meet in Casablanca and she explains that she had returned to her husband, Victor, whom she had believed dead before getting together with Rick.

In The Dark Knight, the love interest writes Bruce Wayne a letter about how she is going to marry Harvey Dent and that she'll always be with him as a friend. However, after her death, Alfred burns it before Bruce can read it.

It's a relatively minor but still tragic instance of Poor Communication Kills: Bruce assumes she was going to leave Harvey for him.

In Dumb and Dumber, Harry got one of these from Fraida Felcher, mistakenly referring to it as a "John Deere" letter. It's obvious to everyone (even Harry himself) that she was cheating on him with Lloyd, though he feigned ignorance until the end of the movie.

In The Thin Red Line (1998), one of the protagonists (Private Bell) tells anyone around him how he really loves his wife (and so won't cheat on her with the local Ladies of Negotiable Virtue). In a (possibly unintentional) hilarious moment, about halfway through the film, he then receives a Dear John letter from his wife about how she's found a new love.

Obviously, Dear John.

Micheal in Siege of the Dead gets one of these just before the start of the movie and is hoping to patch things up. Things don't turn out quite as planned.

John in Goodbye Pork Pie finds one from Sue in his typewriter, which simply reads "Dear John".

In Kill List, Gal says that he woke up to find a "Dear John taped to me cock".

The Goodbye Girl opens with Paula coming home to the apartment she shares with Tony and finding out that, instead of them moving together to California as they'd planned, he is breaking up with her and has left to Europe to film a Bernardo Bertolucci movie. What he fails to mention is that he's sublet their apartment to a man she doesn't know, fellow actor Elliot, which kicks off the plot as Paula and Elliot wind up rooming together.

Literature

In Robert A. Heinlein's If This Goes On —, John Lyle gets a literal Dear John letter. It's briefly depressing before he realizes that he can't remember her that well anyway.

A literal example with John Bell in The Thin Red Line.

Played with in the novel Starship Troopers. When at OCS Johnny claims he and Carmen were dating, but she sent him a "Dear John". This is technically true, since he and Carmen went on a few dates, nothing serious, and she always begins her (occasional) letters with "Dear John". Essentially, Johnny is playing up the trope to gain some street cred.

This trope appeared in a story written by the Polish writer Jarosław Grzędowicz, where a Pole who went work to England was completely devastated when his girlfriend sent him such a letter. A few years later, it appeared in a novel written by his wife, Maja Kossakowska, but American marine in the book has found it quite amusing. Having to endure weeks of torture, having his legs broken, and getting a bullet in the lungs could have something to do with it.

In one short story in the Honor Harrington universe Commissar Yuri Radamacher comments that he spends more time helping heartbroken naval personnel deal with "Dear John" or "Dear Jane" letters than he does actively trying to seek out disloyalty.

In Poul Anderson's "The Corkscrew Of Space", Magarac had gotten one and no longer awaited a letter from his girl.

A double-subversion in The Winds of War. Rhoda writes this to Victor but after hearing of Pearl Harbor writes a second letter asking him to forget it. However later she goes through with it. Leaving Victor feeling free to remarry a woman he had developed feelings for but had just barely forced himself to turn down.

Vivienne's first boyfriend in The Spy Who Loved Me broke up with her with a letter that revealed that he was "semi-engaged" to someone else, essentially telling her that she was just a summer fling.

Live Action TV

In Smallville, Whitney gets a video Dear John letter from Lana so that she can pursue Clark. Ironically, Lana later pulls a repeat performance of this on Clark at the end of Season 7.

Radar's sweetheart dumps him (the message comes in the form of a 45 RPM record), so his friends try to set him up with someone else to help him get over it.

Later, there's one from Frank's wife announcing she plans to divorce him (she'd heard about his affair with Margaret).

When Klinger got one from his wife, it was the one time he tried to get hardship leave when he wasn't scamming.

At least a few times a season, a GI of the week got a Dear John letter. An Italian is distraught upon receiving a "Dear Giovanni" letter.

And once it was Subverted: a blinded GI in post-op asked Father Mulcahy to read his mail to him and the first one, from his girlfriend, started "Dear John..." That was his name.

Subverted again when a pilot only known as Cowboy abducts Colonel Blake to extort a discharge to see his wife, whom he believes is unfaithful. Cowboy clears up the first two warning flags (the Reno return address and the literal "Dear John" first line) by saying that's where he lives and his real name, respectively. They go on, revealing that the letter is her affirmation of her love for him. Cowboy lands and everything is sorted out.

One of the instances in the series has a soldier patient getting a Dear John letter written in a callous tone with a demand for her old photo back. The staff decide to help the soldier by packaging various photos of women gathered from around the camp along with an insulting letter telling her he's forgotten what she even looks like and to pick out which one is hers. The soldier caps it off by suggesting they send the whole parcel "postage due".

Gibbs from NCIS, when asked if he's ever gotten a love letter in Season Two, asks if a "Dear John" counts.

Joel from Northern Exposure gets one of these from his fiancee in the season 2 premiere.

In Power Rangers Zeo, Tommy got such a letter from Kimberly, which successfully sunk their canon couple status to allow writers pair him with Katherine. The amount of fanfics this spawned qualifies it for PR's most infamous Fandom-Specific Plot.

Peyton does this to Mac on CSI NY-she didn't think they could work out the distance issues since she was working in New York but her home was in London, and likely figured Mac was still mourning his late wife. she did return for one episode later on and apologized, saying he deserved better than a note.

The storyline the Porridge episode "Heartbreak Hotel" is Godber getting a letter from his girlfriend Denise.

On a Saved By the Bell: The New Class episode, Screech receives one of these. The kids set him up with another girl to help get him over it.

In the Star Trek: Voyager episode "Hunters," Janeway gets one from her (former) fiancée, telling her that he got married. Justified, though, as she and her crew had been declared dead after disappearing from the Alpha Quadrant and had only recently reestablished contact with Earth.

The Taylor Swift song "Dear John" is a subversion of this trope. Even though the narrator is ending the relationship, the song reveals that she was involved in an unhealthy relationship with an older man, who it's implied took advantage of her and broke her heart. Thus the song is a six minute long "The Reason You Suck" Speech.

A sarcastic reading of a Dear John letter by its recipient comprises the entire lyrics of "Your Woman" by White Town, a UK #1 single in 1997.

The front cover of the final Led Zeppelin album, 'In Through the Out Door', portrays several different perspectives of the same scene at a bar of a man burning a 'Dear John' letter in an ashtray. The last song on that album, I'm Gonna Crawl, would seem to be written from this perspective.

Probably the original "Dear John" song: "A Dear John Letter," first recorded in the 1950s by Ferlin Husky and Jean Shepard and later covered by Pat Boone. Stan Freberg parodied it as "A Dear John and Marsha Letter."

"Good" by Better Than Ezra is about the singer finding one. We only hear one line from it: "It was good living with you."

"Postcard From Pasadena" by Gord Bamford. His girlfriend runs off with a tall dark stranger and breaks the news to him by sending a postcard that says, "Don't call, I'll call you."

The narrator of Colin Raye's "Little Red Rodeo" discovers a Daar John letter written by his girlfriend, who is leaving because he can't commit. This prompts a Race for Your Love, in which he goes to track her down, showing her photograph and asking people if they've seen his love with "Texas plates, candy apple red Rodeo."

Newspaper Comics

Gary Larson made a The Far Side cartoon of two male deer in a forest, one holding a letter. "My God! She left me a John Deer letter!"

"Dearest Helena, By now the news of our defeat has reached the Earth. The creatures we were sent here to tame are un-tamable, and the colonies we were sent to reclaim have proven to be stronger than we anticipated. Whatever you may hear about what has happened out here, know this; Alexei did not die gloriously in battle. I killed him. My pride killed him. And now my pride has consumed me as well. You will never see me again, Helena. Tell our children that I love them, and that their father died in defense of their future. Au revoir."

In Katawa Shoujo, main character Hisao receives one from his old sort-of girlfriend Iwanako part way through the story. The way he reacts to it is different in each route depending on how he's changed through his current relationship, though in all of them it causes a barrel full of mixed feelings and introspection on his part.

In Mass Effect 3 a human woman ponders to do this to her serving husband, leaving him for her asari mistress. And then begins to get second thoughts when the Asari starts backpedaling at the thought of them being in a serious long-term relationship.note Of course "long term" for an Asari is totally different from "long term" for a human.

Jason Hudson from Call of Duty: Black Ops received one at some point before the game. Players that can figure out the password to his account on the terminal hidden in the main menu can read it themselves.

Webcomics

In General Protection Fault, Nick is abducted by Ki's Evil Counterpart from a parallel universe the night before he is to marry her, and his counterpart leaves behind a letter saying he can't marry her, but Ki refuses to believe it and eventually enters the dimension on a rescue mission. The letter is even called a "Dear John" Letter

In Split Screen. Jan assumes this is what Jeremy gave her when he snuck out on her. Stubborn pride caused her to not read the letter for a whole year, where she found out it was a love confession and an explanation as to why he did what he did. It Makes Sense in Context.

For an extra punch to his (and the audience's) gut, she taped it over their wedding video, so immediately after she's done, it cuts to them dancing at their wedding. Ouch.

On King of the Hill, Bill's wife Lenore left him without any notice, leading him to cling to the belief she would return for years. He eventually snaps in the episode "Pretty, Pretty Dresses" and (in his mind) tells Lenore off for abandoning him, saying that he was at least worth a Dear John letter.

On The Looney Tunes Show, Lola learns the concept of a Dear John letter from a movie. Later, Bugs leaves a note to a mechanic named John on his broken microwave, reading "Dear John: This isn't working." Lola sees the note, assumes it's addressed to her (never mind that it doesn't say "Dear Lola", but that's Lola for you) and leaves to a monastery to find inner peace. But before she leaves, she catches a cockroach trying to enter her apartment, so she leaves a note for all bugs to go away. Naturally, Bugs sees a note reading "Dear Bugs: I don't want to ever see you again" and assumes the worst.

In an Al Brodax Popeye cartoon, Popeye's trained fleas fly the coop on a passing dog. They leave him a Dear John letter which ends with "Help!".

The Fleischer shorts "I Never Changes My Altitude" and "Me Feelins is Hurt" have these too.

In The Flintstones movie "I Yabba-Dabba-Do!", Pebbles thought she was getting one of these from Bamm-Bamm, but it was really a love letter ending with him proposing.

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